The most infamous thing like this is probably Contad Veidt's character in the 1928 film "The Man Who Laughs". The imagery is said to have inspired Batman's Joker; and the artistic similarities are a bit uncanny.

The most infamous thing like this is probably Contad Veidt's character in the 1928 film "The Man Who Laughs". The imagery is said to have inspired Batman's Joker; and the artistic similarities are a bit uncanny.